Methacrylic Acid → Phenoxyethylmethacrylate methylmethacrylate methacrylic acid

HRID 446625

Reaction equation

HRID 446625 reaction equation
[C:1]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:16]([OH:21])(=[O:20])[C:17]([CH3:19])=[CH2:18].[C:22]([O:27][CH3:28])(=[O:26])[C:23]([CH3:25])=[CH2:24]>COC(=O)C(N=NC(C)(C)C(OC)=O)(C)C.C(C(C)=O)C>[C:1]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:22]([O:27][CH3:28])(=[O:26])[C:23]([CH3:25])=[CH2:24].[C:16]([OH:21])(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 663572-Phenoxyethyl methacrylate

Product 1

HCID 67403649Phenoxyethylmethacrylate methylmethacrylate methacrylic acidYield 162.8%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolvent3×HCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)Solvent2×

Conditions

Temperature
72 °C

Procedure

To a 1000-ml three-neck flask equipped with a stirrer and a condenser, 88 g of methyl ethyl ketone was added, and then heated to 72° C. under a nitrogen atmosphere. To this flask, a solution in which 0.85 g of dimethyl-2,2′-azobisisobutyrate, 50 g of phenoxyethyl methacrylate, 13 g of methacrylic acid, and 37 g of methyl methacrylate were dissolved in 50 g of methyl ethyl ketone was added dropwise over 3 hours. After completion of the dropwise addition, the content in the flask was allowed to react for an additional one hour, and then, a solution in which 0.42 g of dimethyl-2,2′-azobisisobutyrate was dissolved in 2 g of methylethyl ketone was added thereto, the temperature of the mixture was raised to 78° C., and the mixture was heated for 4 hours. The resulting reaction solution was subjected to re-precipitation twice with an excess amount of hexane, and the precipitated resin was dried and 96.5 g of phenoxyethyl methacrylate/methyl methacrylate/methacrylic acid (copolymerization ratio [% by mass ratio]=67/20/13) copolymer (resin dispersant P-1) was obtained.

Workup

  1. customTo a 1000-ml three-neck flask equipped with a stirrer and a condenser
  2. additionwas added dropwise over 3 hours
  3. additionAfter completion of the dropwise addition
  4. customto react for an additional one hour
  5. additionwas added
  6. temperaturethe temperature of the mixture was raised to 78° C.
  7. temperaturethe mixture was heated for 4 hours
  8. customThe resulting reaction solution
  9. customwas subjected to re-precipitation twice with an excess amount of hexane
  10. customthe precipitated resin was dried

Sources & evidence

ORD record
ord-a9f1788e630c46819301a9498866b30c
Source dataset
uspto-grants-2013_07
Patent number
US08480223B2

Linked notes

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